Enantioselective Hydroesterificative Cyclization of 1,6-Enynes to Chiral γ-Lactams Bearing a Quaternary Carbon Stereocenter

Ren, Xinyi; Tang, Lin; Shen, Chaoren; Li, Huimin; Wang, Peng; Dong, Kaiwu

doi:10.1021/acs.orglett.1c00952

Cited by 18 publications

(13 citation statements)

References 58 publications

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“…This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC, [35] HOTZOH, [36] PEQVOZ [37] and USAJIK. [38] In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the I•••CH2=C distances are in the range of 3.526-3.692 Å (Figure S1). In the XB-based azobenzene, a short distance exists between the negative equatorial region of iodine atom and carbon of the electron deficient fluorinated group (I•••C2 distance = 3.652 Å).…”

Section: X-ray Structure Analysis Of Xb Azobenzenesmentioning

confidence: 88%

“…X-ray structure of I-azo-NH-MMA developing undulating parallel chains due to C•••I halogen bonds This intriguing contact convinced us to make a Cambridge Structural Database (CSD version 5.42 updates, Sep 2021) analysis on the interaction between an iodine and a double bond (I•••CH2=C). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC,[35] HOTZOH,[36] PEQVOZ[37] and USAJIK [38]. In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the…”

mentioning

confidence: 93%

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Multi Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Frangville¹,

Kumar²,

Gelbcke³

et al. 2021

Preprint

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Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye I-azo-NO2, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As concern parent I-azo-NH-MMA, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures with the same I···CH2=C contact. For all compounds, a 19F NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, intermediate I-azo-NO2 also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design multi-stimuli responsive materials for highly functional devices.

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Section: X-ray Structure Analysis Of Xb Azobenzenesmentioning

confidence: 88%

mentioning

confidence: 93%

Multi Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Frangville¹,

Kumar²,

Gelbcke³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC [35], HOTZOH [36], PEQVOZ [37] and USAJIK [38]. In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the I•••CH 2 =C distances are in the range of 3.526-3.692 Å (Figure S1, Supplementary Materials).…”

Section: Table 2 Parameters Of Halogen and Hydrogen Bonds Inmentioning

confidence: 99%

“…This intriguing contact convinced us to make a Cambridge Structural Database (CSD version 5.42 updates, Sep 2021) analysis on the interaction between an iodine and a double bond (I•••CH 2 =C, C•••I distances between 3.0 and 4.0 Å). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC[35], HOTZOH[36], PEQVOZ[37] and USAJIK[38]. In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the I•••CH 2 =C distances are in the range of 3.526-3.692 Å (FigureS1, Supplementary Materials).…”

mentioning

confidence: 99%

Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Frangville¹,

Kumar²,

Gelbcke³

et al. 2021

Molecules

View full text Add to dashboard Cite

Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye I-azo-NO2, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As far as compound I-azo-NH-MMA is concerned, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures showing the same I···CH2=C contact. For all compounds, an 19F-NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, the intermediate I–azo–NH2 also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design future multi-stimuli responsive materials for highly functional devices.

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“…The transition metal-catalyzed stereoselective cyclization of 1,6-enynes provides efficient and convenient access to five-membered (hetero)cycles [66]. Recently, Dong and coworkers [67] developed a Pd-catalyzed enantioselective hydroesterification-cyclization reaction of amide-tethered 1,6-enynes (Scheme 28). Using as catalyst system the combination of Pd(OAc) 2 , (S)-MeOBIPHEP, and TsOH•H 2 O, a series of chiral carboxylic esters containing the γ-lactam skeleton and an all-carbon quaternary carbon stereocenter were synthesized with 69%-95% ee values for the enantioselectivity.…”

Section: Palladium-catalyzed Carbonylation Of Enynesmentioning

confidence: 99%

Palladium-catalyzed enantioselective carbonylation reactions

Peng

Liu

et al. 2022

Sci. China Chem.

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Carbonylation, one of the most powerful approaches to the preparation of carbonylated compounds, has received significant attention from researchers active in various fields. Indeed, impressive progress has been made on this subject over the past few decades. Among the various types of carbonylation reactions, asymmetric carbonylation is a straightforward methodology for constructing chiral compounds. Although rhodium-catalyzed enantioselective hydroformylations have been discussed in several elegant reviews, a general review on palladium-catalyzed asymmetric carbonylations is still missing. In this review, we summarize and discuss recent achievements in palladium-catalyzed asymmetric carbonylation reactions. Notably, this review’s contents are categorized by reaction type.

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Enantioselective Hydroesterificative Cyclization of 1,6-Enynes to Chiral γ-Lactams Bearing a Quaternary Carbon Stereocenter

Cited by 18 publications

References 58 publications

Multi Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Multi Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Palladium-catalyzed enantioselective carbonylation reactions

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